There are a variety of factors that lead to a character we consider The Woobie.

Trope side

Consistency of Suffering: It's clear that the suffering the character goes through should be frequent or continuous, the former more commonly for serial and the latter more commonly for standalone works. Characters who are one-shot or infrequent recurring characters in serial works would more likely follow the "continuous" rule. Basically, frequency is when you add up all the events or even all the major bad events, they add up to something huge, while continuity is where the suffering is the status quo. It is certainly possible to have both at once. Of course, this alone is not very different from a regular Butt Monkey.

External Circumstances: A character who suffers as a result of his own actions is not the woobie. So, for example, if a character has to live with the consequences of doing something bad (such as cheating) or stupid, provided he was warned, (such as charging right into a dangerous battle), he is not a woobie. Important Note: Being too afraid, weak, or self-defeating to prevent someone from hurting you is different from causing your own problems. Not only are all of these flaws sympathetic enough that they add to woobie-status rather than subtracting from it, but may have been caused by the same or other attackers in the first place indirectly, especially if they are highly influential like Abusive Parents.

The "Just Deserts" Test: A character who is actively cruel to others cannot be a regular woobie by default. What differentiates a Jerkass Woobie from a regular Jerkass is how well their suffering justifies their actions or vice versa. This is often a matter of opinion, especially when the Designated Monkey reaction is involved. If the suffering does not justify the actions or the actions justify the suffering, he's probably not a Jerkass Woobie. On the other hand, if the actions do not justify the suffering and the suffering justifies the actions, he probably is.

Power and Other Factors: The best woobies tend to be characters without any power such as someone discriminated against by everyone else, children in abusive families, underlings always on the edge of losing their job, or characters who always fall victim to bad luck no matter what they do. Too much power (such as being a strong matriarch, or able to outwit authority figures) diminishes the sympathy since the audience is sure they can take care of themselves. Sympathetic flaws like weakness (physical or emotional), self-defeating behavior, and proneness to emotions such as sadness and anxiety over ones like excitement and anger will not make the status on their own usually, but can be hugely beneficial in pushing a questionable character over the line. A character who is extremely virtuous—kind, honest, loyal, etc.—who also suffers heavily is also a more likely woobie than one who isn't.

What seems a little tricky about this is the idea that the fandom feels sorry for the character. Now, unless the show is a Sugar Bowl (or, for a particularly unlucky woobie, a Sugar Bowl except for this one guy's bad life), and sometimes even then, the audience will feel sorry for most if not all of the characters at one point or another. People have specified feeling sorry for the resident Jerkass in the episode they were watching only. Clearly, this alone is not enough to make the character a woobie. So what is the difference?

Take for instance, Alice and Bob. Alice has lots of great friends and Bob has never had any despite trying to make them for years. Then one day Alice loses all her friends due to a misunderstanding and gets them back by the end of the episode. Meanwhile, Bob still doesn't get any friends. Now, when the audience is watching Alice, they would likely say something to the effect of "I felt bad for Alice when..." When the topic turns to Bob, the audience members would likely say something closer to "I feel sorry for Bob because..." The main difference between these two is the conditionality of the sympathy. For Alice, the sympathy is conditional—it's fleeting, temporal, in the moment. For Bob, it's unconditional—consistent, steadfast, forever.

Another important factor is whether it's personalized. Suppose your show takes place during a great war and plenty of hardships are had by everyone. They can't all be the woobie, but what about the one who went through a succession of abusive parents and then nearly died due to ostracism? This is heavy suffering even for the universe, and so the character stands out even in one of the bleaker worlds.

Uses for a woobie

One potential use for a woobie include making other characters look evil. Villains who attack the hero are just trying to win their fight. Villains who attack The Woobie are cowards at best, bullying monsters at worst. Oh, and if the character is the primary reason another is The Woobie? They'll most likely be hated, perhaps in a good way.

Another is to provide a tragic contrast; kind of a weird opposite of comic relief. And of course, sometimes they're used just to show how messed up the world is as a whole. Some are intended to be in-universe woobies, particularly Littlest Cancer Patients like Tiny Tim (who, in a surprisingly effective way, had a curable illness), in order to tug at the heartstrings of other characters as well as the audience. Unfortunately, sometimes, this will lead to the character becoming a Sympathetic Sue, or just to Darkness-Induced Audience Apathy.

Generally speaking, piling loads of crap onto the character will turn him into The Woobie particularly if he has traits such as kindness, a large number of sympathetic flaws, and powerlessness. But at some point there's just too much. How to avoid DIAA and Sympathetic Sue accusations?

The most important rule is Show, Don't Tell. There are a few effects of this. Since we see bad things happen, we understand they're plausible for the universe. Another thing that's helpful is seeing how much it hurts. Another implication is to use tragic backstory sparingly. Tragic backstory is great for making a character The Woobie quickly, but it has to have some lasting effects, otherwise it comes across as the author's refusal to put the character through hell, and insistence that he has done so anyway. Sometimes tragic backstory can be used to make a character who would have been a woobie anyway, even more of a woobie. For instance, if your character is saying that today is the best day he's ever had and even that day is punctuated by obviously pitiful moments, that character will almost certainly become a woobie.

One issue with Sympathetic Sues is that they almost always violate Show, Don't Tell. At some point, whining about backstory gets old. Show some substance in the moment, and you should get the desired result.

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